Download citation
Download citation
link to html
The title mol­ecule, C3H7NO4, adopts a nearly symmetric conformation. The crystal structure is stabilized by inter­molecular O—H...O hydrogen bonds, linking the mol­ecules to form a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021866/hk2051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021866/hk2051Isup2.hkl
Contains datablock I

CCDC reference: 613719

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.086
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.56 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.23 From the CIF: _reflns_number_total 597 Count of symmetry unique reflns 597 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-Nitropropane-1,3-diol top
Crystal data top
C3H7NO4Dx = 1.445 Mg m3
Mr = 121.10Melting point: 327.15 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1246 reflections
a = 10.331 (3) Åθ = 3.8–23.1°
b = 6.322 (2) ŵ = 0.14 mm1
c = 8.520 (3) ÅT = 294 K
V = 556.5 (3) Å3Prism, colorless
Z = 40.24 × 0.20 × 0.18 mm
F(000) = 256
Data collection top
Bruker SMART CCD area-detector
diffractometer
597 independent reflections
Radiation source: fine-focus sealed tube505 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.2°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1012
Tmin = 0.968, Tmax = 0.976k = 76
2868 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.0466P]
where P = (Fo2 + 2Fc2)/3
597 reflections(Δ/σ)max < 0.001
79 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.14 e Å3
Special details top

Experimental. 1H NMR (DMSO-d6, δ, p.p.m.): 3.62 (t, 4H), 4.56 (q, 1H), 5.09 (t, 2H).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8876 (2)0.7482 (4)0.4725 (3)0.0769 (7)
O20.7428 (2)0.5568 (3)0.5828 (4)0.0803 (7)
O30.63039 (17)1.0546 (3)0.5997 (3)0.0601 (6)
H30.582 (4)1.007 (6)0.672 (6)0.090*
O40.99210 (18)0.6747 (3)0.8253 (3)0.0610 (6)
H40.945 (4)0.610 (6)0.904 (6)0.091*
N10.8136 (2)0.7103 (3)0.5793 (3)0.0493 (6)
C10.7585 (3)1.0710 (4)0.6550 (4)0.0460 (6)
H1A0.76191.17420.73910.055*
H1B0.81381.12070.57070.055*
C20.8090 (2)0.8610 (4)0.7146 (3)0.0378 (5)
H20.74930.80600.79410.045*
C30.9433 (2)0.8754 (4)0.7846 (3)0.0484 (6)
H3A1.00100.94150.70940.058*
H3B0.94050.96410.87750.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0849 (15)0.0957 (17)0.0500 (12)0.0133 (14)0.0215 (13)0.0177 (12)
O20.0934 (15)0.0493 (12)0.0981 (19)0.0177 (12)0.0066 (16)0.0129 (13)
O30.0476 (11)0.0719 (13)0.0609 (13)0.0000 (9)0.0076 (10)0.0244 (12)
O40.0501 (11)0.0806 (14)0.0523 (12)0.0221 (9)0.0064 (9)0.0175 (12)
N10.0517 (12)0.0443 (12)0.0521 (14)0.0015 (10)0.0046 (11)0.0032 (11)
C10.0456 (14)0.0426 (12)0.0499 (14)0.0003 (10)0.0005 (11)0.0053 (11)
C20.0370 (11)0.0410 (11)0.0355 (11)0.0001 (10)0.0049 (10)0.0006 (11)
C30.0416 (13)0.0586 (14)0.0449 (13)0.0023 (12)0.0011 (12)0.0002 (12)
Geometric parameters (Å, º) top
O1—N11.213 (3)C1—C21.514 (3)
O2—N11.215 (3)C1—H1A0.9700
O3—C11.409 (3)C1—H1B0.9700
O3—H30.85 (5)C2—C31.512 (3)
O4—C31.409 (3)C2—H20.9800
O4—H40.92 (5)C3—H3A0.9700
N1—C21.496 (3)C3—H3B0.9700
C1—O3—H3109 (3)N1—C2—C1108.1 (2)
C3—O4—H4113 (2)C3—C2—C1113.3 (2)
O1—N1—O2123.8 (3)N1—C2—H2109.0
O1—N1—C2118.2 (2)C3—C2—H2109.0
O2—N1—C2118.0 (2)C1—C2—H2109.0
O3—C1—C2111.8 (2)O4—C3—C2111.8 (2)
O3—C1—H1A109.3O4—C3—H3A109.3
C2—C1—H1A109.3C2—C3—H3A109.3
O3—C1—H1B109.3O4—C3—H3B109.3
C2—C1—H1B109.3C2—C3—H3B109.3
H1A—C1—H1B107.9H3A—C3—H3B107.9
N1—C2—C3108.3 (2)
O1—N1—C2—C358.1 (3)O3—C1—C2—N163.8 (3)
O2—N1—C2—C3121.9 (3)O3—C1—C2—C3176.3 (2)
O1—N1—C2—C165.0 (3)N1—C2—C3—O454.6 (3)
O2—N1—C2—C1115.1 (3)C1—C2—C3—O4174.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.92 (5)1.88 (5)2.765 (3)161 (4)
O3—H3···O4ii0.85 (5)1.97 (5)2.800 (3)165 (4)
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x1/2, y+3/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds